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5‐Hydroxymethylfurfural Derivative Based Thermoplastic Elastomers Synthesized via Thiol‐Michael Addition Reaction Utilizing Poly(lactic acid) as Hard End Blocks
Author(s) -
Zhang Daihui,
Dumont MarieJosée
Publication year - 2018
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201800039
Subject(s) - polymer chemistry , gel permeation chromatography , acrylate , ultimate tensile strength , diol , maleimide , thermoplastic elastomer , materials science , michael reaction , thermoplastic , coupling reaction , chemistry , copolymer , organic chemistry , composite material , polymer , catalysis
5‐Hydroxymethylfurfural derivative based thermoplastic elastomers (TPEs) are efficiently synthesized via a two‐step thiol‐Michael addition reaction using polylactide (PLA) as the hard segments in a one‐pot reaction under mild conditions. The first step involves the synthesis of prepolymers having thiol groups as end groups. The macromolecular coupling reaction which occurs between the prepolymers and the PLA having acrylate‐end groups is demonstrated via 1 H NMR and gel permeation chromatography (GPC). Additionally, by varying the ratio of 1,3‐propanedithiol and 2,5‐furan diacrylate, TPEs with soft segments having different molecular weights are synthesized, and then characterized. The cyclic tensile tests demonstrate the elasticity of the synthesized TPEs. Furthermore, the Diels–Alder reaction is used to dynamically crosslink the soft segments in the TPEs, leading to the increased mechanical properties in terms of Young's modulus and tensile strength.